Effects of plant sulfur nutrition on acrylamide and aroma compounds in cooked wheat

Wheat flour from plants deficient in sulfur has been shown to contain substantially higher levels of free amino acids, particularly asparagine and glutamine, than flour from wheat grown where sulfur nutrition was sufficient. Elevated levels of asparagine resulted in acrylamide levels up to 6 times higher in sulfur-deprived wheat flour, compared with sulfur-sufficient wheat flour, for three varieties of winter wheat. The volatile compounds from flour, heated at 180 degrees C for 20 min, have been compared for these three varieties of wheat grown with and without sulfur fertilizer. Approximately 50 compounds were quantified in the headspace extracts of the heated flour; over 30 compounds were affected by sulfur fertilization, and 15 compounds were affected by variety. Unsaturated aldehydes formed from aldol condensations, Strecker aldehydes, alkylpyrazines, and low molecular weight alkylfurans were found at higher concentrations in the sulfur-deficient flour, whereas low molecular weight pyrroles and thiophenes and sugar breakdown products were found at higher concentrations in the sulfur-sufficient flour. The reasons for these differences and the relationship between acrylamide formation and aroma volatile formation are discussed.     

Formation of Strecker aldehydes and pyrazines in a fried potato model system

Sugars and amino acids were removed from potato slices by soaking in water and ethanol. They were then infused with various combinations of sugars (glucose and/or fructose) and amino acids (asparagine, glutamine, leucine, isoleucine, phenylalanine, and/or methionine) and fried. Volatile compounds were trapped onto Tenax prior to gas chromatography-mass spectrometry. Relative amounts of compounds (relative to the internal standard) and relative yields (per mole of amino acid infused into the slices) were determined. Amounts of 10 pyrazines, 4 Strecker aldehydes, and 4 other compounds were monitored. Relative amounts and relative yields of compounds varied according to the composition of the system. For the single amino acid-glucose systems, leucine gave the highest relative amount and relative yield of its Strecker aldehyde. Asparagine and phenylalanine gave the highest total relative amount and total relative yield, respectively, of pyrazines. In the system containing all of the amino acids and glucose, the relative amount of 3-methylbutanal was higher, whereas the amounts of the other monitored Strecker aldehydes were lower. Most of the relative amounts of individual pyrazines were lower compared to the glucose-asparagine system, whereas the total relative yield of pyrazines was lower, compared to all of the single amino acid-glucose mixtures. Addition of fructose to the mixed amino acid-glucose model system generated Strecker aldehydes and pyrazines in ratios that were more similar to those of untreated potato chips than to those from the same system but without fructose. Both the sugars and the amino acids present in potato are crucial to the development of flavor compounds in fried potato slices.     

Influence of sulfur amino acids on the volatile and nonvolatile components of cooked salmon (Salmo salar)

Volatile and nonvolatile compounds, which could contribute to flavor, were analyzed in salmon. One hundred twenty-three volatile compounds were identified in the headspace of two different samples of cooked salmon, including lipid-derived volatiles, Maillard-derived volatiles, sulfur volatiles, Strecker aldehydes, nitrogen heterocyclic compounds, terpenes, and trimethylamine. Significant differences between samples were found for 104 of the volatiles. Although the levels of free cysteine and methionine were low in the salmon, sulfur volatiles were formed in the cooked fish, demonstrating that there were sufficient sulfur amino acids present for their formation. Notable differences in sulfur compounds between the samples suggested that small changes in sulfur amino acids could be responsible. When this hypothesis was tested, salmon heated with cysteine had increased levels of many thiophenes, thiazoles, alicyclic sulfides, and nitrogen heterocycles. With the addition of methionine, levels of dimethyl sulfides, two alicyclic sulfides, pyrazines, some unsaturated aldehydes, and alcohols and 2-furanmethanethiol increased. The largest difference found among the nonvolatile (low molecular weight water-soluble) compounds was in inosine monophosphate.     

Analysis of volatiles in meat from Iberian pigs and lean pigs after refrigeration and cooking by using SPME-GC-MS

The volatile compounds generated in meat from Iberian and lean pigs after four different treatments (raw, refrigerated, cooked, and refrigerated cooked meat) were analyzed. The different treatments showed different volatile profiles. Methyl alcohols and ketones (such as 2-ethyl-hexan-1-ol, 2-methyl-butan-1-ol, 3-methyl-butan-1-ol, and 3-hydroxy-butan-2-one) were the most representative in refrigerated meat because of the degradation of carbohydrates and proteins together with the Strecker degradation pathway. Lipid-derived volatiles were the most abundant in cooked meat and refrigerated cooked meat. Meat from different pig breeds presented different volatile profiles, probably due to different enzymatic and oxidative deterioration susceptibility. Otherwise, the fat content and its compositional characteristics also played an important role in the generation of volatiles. As compared to samples from lean pigs, muscles from Iberian pigs showed a higher content of heme iron that may have promoted the generation of higher content of total lipid-derived volatiles during the refrigeration of cooked meat. Despite that, the formation of volatiles with low thresholds and related to intense rancidity perception likely to be derived from polyunsaturated fatty acids was higher in lean pork than in meat from Iberian pigs. This might be expected to lead to a more intense development of a warmed over flavor during refrigeration of cooked samples from lean pigs.     

Reducing acrylamide precursors in raw materials derived from wheat and potato

A review of agronomic and genetic approaches as strategies for the mitigation of acrylamide risk in wheat and potato is presented. Acrylamide is formed through the Maillard reaction during high-temperature cooking, such as frying, roasting, or baking, and the main precursors are free asparagine and reducing sugars. In wheat flour, acrylamide formation is determined by asparagine levels and asparagine accumulation increases dramatically in response to sulfur deprivation and, to a much lesser extent, with nitrogen feeding. In potatoes, in which sugar concentrations are much lower, the relationships between acrylamide and its precursors are more complex. Much attention has been focused on reducing the levels of sugars in potatoes as a means of reducing acrylamide risk. However, the level of asparagine as a proportion of the total free amino acid pool has been shown to be a key parameter, indicating that when sugar levels are limiting, competition between asparagine and the other amino acids for participation in the Maillard reaction determines acrylamide formation. Genetic approaches to reducing acrylamide risk include the identification of cultivars and other germplasm in which free asparagine and/or sugar levels are low and the manipulation of genes involved in sugar and amino acid metabolism and signaling. These approaches are made more difficult by genotype/environment interactions that can result in a genotype being "good" in one environment but "poor" in another. Another important consideration is the effect that any change could have on flavor in the cooked product. Nevertheless, as both wheat and potato are regarded as of relatively high acrylamide risk compared with, for example, maize and rice, it is essential that changes are achieved that mitigate the problem.     

Mechanisms of alkylpyrazine formation in a potato model system containing added glycine

The use of glycine to limit acrylamide formation during the heating of a potato model system was also found to alter the relative proportions of alkylpyrazines. The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alkylpyrazines which increased in the presence of glycine had at least one 13C-labeled methyl substituent derived from glycine. The distribution of 13C within the pyrazines suggested two pathways by which glycine, and other amino acids, participate in alkylpyrazine formation, and showed the relative contribution of each pathway. Alkylpyrazines that involve glycine in both formation pathways displayed the largest relative increases with glycine addition. The study provided an insight into the sensitivity of alkylpyrazine formation to the amino acid composition in a heated food and demonstrated the importance of those amino acids that are able to contribute an alkyl substituent. This may aid in estimating the impact of amino acid addition on pyrazine formation, when amino acids are added to foods for acrylamide mitigation.     

On-line MS/MS monitoring of acrylamide generation in potato- and cereal-based systems

An on-line MS/MS technique was used to study the generation of acrylamide in rye-, wheat-, and potato-based systems during cooking. Acrylamide release to the gas phase was monitored continuously and was correlated with the acrylamide content of samples using a calibration based upon the partition of [1,2,3-(13C3)]acrylamide. On-line results at 180 degrees C were compared with data relating to the same systems obtained through GC-MS analysis. Agreement between the two techniques was notable, both in terms of the temporal profiles of acrylamide generation and when comparing the relative magnitudes of results for potato, wheat, and rye determined by each method. The effects of pH (citric acid) and added amino acids (soy protein hydrolysate) on the generation of acrylamide in hydrated potato flake were modeled at 180 degrees C. It was concluded that a combined treatment of low levels of each additive could result in significant reductions in acrylamide, although the effects of such treatments on sensory properties such as color and flavor remain to be evaluated.     

Changes in free amino acids and sugars in potatoes due to sulfate fertilization and the effect on acrylamide formation

To examine how sulfur deprivation may affect acrylamide formation in cooked potatoes, three varieties of potato were grown under conditions of either severe sulfur deprivation or an adequate supply of sulfur. In all three varieties sulfur deprivation led to a decrease in acrylamide formation, even though the levels of sugars, which are acrylamide precursors, were higher in tubers of the sulfur-deprived plants. In one variety the concentration of free asparagine, the other precursor for acrylamide, was also higher. There was a very close correlation between the concentration of asparagine in the tubers expressed as a proportion of the total free amino acid pool and the formation of acrylamide upon cooking, whereas sugars were poorly correlated with acrylamide. In potatoes, where concentrations of sugars are usually limiting, competition between asparagine and other amino acids participating in the Maillard reaction may be a key determinant of the amount of acrylamide that is formed during processing.     

Influence of lipids in the generation of phenylacetaldehyde in wort-related model systems

The effect of lipids on the formation of the Strecker aldehyde phenylacetaldehyde during wort boiling was studied to determine the role that small changes in the lipid content of the wort have in the production of significant flavor compounds in beer. Wort was treated with 0-2.77 mmol per liter of glucose, linoleic acid, or 2,4-decadienal and heated at 60-98 degrees C for 1 h. After this time, the amount of the Strecker aldehyde phenylacetaldehyde increased in the samples treated with linoleic acid or decadienal but not in the samples treated with glucose. Thus, the amount of phenylacetaldehyde produced in the presence of linoleic acid was 1.1-2.5 times the amount of the Strecker aldehyde produced in the control wort, and this amount increased to 3.6-4.6 times when decadienal was employed. The higher reactivity of decadienal than linoleic acid for this reaction decreased with temperature and was related to the oxidation of linoleic acid that occurred to a higher extent at higher temperatures. The above results suggest that lipids can contribute to the formation of Strecker aldehydes during wort boiling and that changes in the lipid content of the wort will produce significant changes in the formation of Strecker aldehydes in addition to other well-known consequences in beer quality and yeast metabolism. On the other hand, because of the high glucose content in wort, small changes in its content are not expected to affect the amount of Strecker aldehydes produced.     

Effect of lipid composition on meat-like model systems containing cysteine, ribose, and polyunsaturated fatty acids

This paper compares the volatile constituents of model systems containing the important meat aroma precursors cysteine and ribose, with and without either methyl linoleate, an n-6 fatty acid, or methyl alpha-linolenate, an n-3 acid, both of which are present in meat. Many of the volatile compounds formed from the reaction between cysteine and ribose were not formed, or formed in lower amounts, when lipid was present. This may be due to the reaction between hydrogen sulfide, formed from the breakdown of cysteine, and lipid degradation products. In addition, cysteine and ribose modified lipid oxidation pathways, so that alcohols and alkylfurans were formed rather than saturated and unsaturated aldehydes. Several volatile compounds, which have been found at elevated levels in cooked meat from animals fed supplements high in n-3 acids, were formed when methyl alpha-linolenate reacted with cysteine and ribose. The possible effects of increasing the n-3 content of meat upon flavor formation during cooking are discussed.     

Release and evaporation of volatiles during boiling of unhopped wort

The release and evaporation of volatile compounds was studied during boiling of wort. The observed parameters were boiling time, boiling intensity, wort pH, and wort density. The effect of every parameter was discussed and approached chemically, with an eye on beer-aging processes. The results indicated that pH highly influenced the release of flavor compounds and that the formation of Strecker aldehydes was linear with boiling time. However, because of evaporation of volatiles, information about the applied thermal load on wort is lost when using a volatile heat load indicator. The thiobarbituric acid (TBA) method, which includes the nonvolatile precursors of volatile aging compounds, proved to be a more reliable method to determine all kinds of heat load on wort. Finally, it was discussed how the obtained insights could help to understand the mechanism of beer aging.     

Measurement of acrylamide and its precursors in potato, wheat, and rye model systems

The relationship between acrylamide and its precursors, namely, free asparagine and reducing sugars, was studied in cakes made from potato flake, wholemeal wheat, and wholemeal rye, cooked at 180 degrees C, from 5 to 60 min. Between 5 and 20 min, major losses of asparagine, water, and total reducing sugars were accompanied by large increases in acrylamide, which maximized in all three products between 25 and 30 min, followed by a slow linear reduction. Acrylamide formation did not occur to a large degree until the moisture contents of the cakes fell below 5%. Linear relationships were observed for acrylamide formation with the residual levels of asparagine and reducing sugars for all three food materials.     

Added versus Accumulated Sugars on Color Development and Acrylamide Formation in French-Fried Potato Strips

Added (glucose addition) versus accumulated (in situ sugar development via cold-temperature storage) sugar treatments were investigated in relation to acrylamide formation within fried potato strips at standardized levels of finish-fried color (Agtron color scores ranged from 36 to 84). The added sugar treatment exhibited a relatively reduced rate of acrylamide formation and generally possessed a lower and less variable acrylamide content (61-1290 ng/g) than the accumulated sugar scheme (61-2191 ng/g). In a subsequent experiment, added fructose applied to strip surfaces via dipping prior to frying favored acrylamide formation over color development relative to added glucose, for which the reverse trend was observed. Thus, where acrylamide differences were noted between added and accumulated sugar treatments (given equivalent Agtron color scores), this result was likely aided by the relative higher fructose content in strips of the accumulated sugar scheme rather than simply a greater relative concentration of total reducing sugars.     

Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system

Fruits and vegetables contain naturally occurring polyphenolic compounds that can undergo enzyme-catalyzed oxidation during food preparation. Many of these compounds contain catechol (1,2-dihydroxybenzene) moieties that may be transformed into o-quinone derivatives by polyphenoloxidases and molecular oxygen. Secondary reactions of the o-quinones include the Strecker degradation of ambient amino acids to form flavor-important volatile aldehydes. The purpose of this work was to investigate the mechanism of the polyphenol/o-quinone/Strecker degradation sequence in a nonenzymic model system. By using ferricyanide ion as the oxidant in pH 7.17 phosphate buffer at 22 degrees C, caffeic acid, chlorogenic acid, (+) catechin, and (-) epicatechin were caused to react with methionine and phenylalanine to produce Strecker aldehydes methional and phenylacetaldehyde in 0.032-0.42% molar yields (0.7-10 ppm in reaction mixtures). Also, by employing l-proline methyl ester in a reaction with 4-methylcatechol, a key reaction intermediate, 4-(2'-carbomethoxy-1'-pyrrolidinyl)-5-methyl-1,2-benzoquinone (7), was isolated and tentatively identified.     

Flavor Volatiles of Rice During Cooking Analyzed by Modified Headspace SPME/GC‐MS

The flavor volatiles in three Japanese rice cultivars, Nihonbare, Koshihikari, and Akitakomachi, during cooking were directly extracted by using a modified headspace solid‐phase microextraction (SPME) method and analyzed by gas chromatography‐mass spectrometry (GC‐MS). A total of 46 components were identified, including aldehydes, ketones, alcohols, and heterocyclic compounds, as well as fatty acids and esters, phenolic compounds, hydrocarbons, etc. The amount of key odorant compounds increased with cooking, while the amount of low‐boiling volatiles decreased. The similarities and differences of the three rice cultivars were determined through a comparison of their volatile components. Nihonbare was characterized by a higher amount of indole but an absence of the chemical class of fatty acid esters. In contrast, both Koshihikari and Akitakomachi had a higher amount of 4‐vinylphenol and an abundance of those esters. Koshihikari and Akitakomachi were quite similar in regard to those flavor volatiles. Furthermore, the observations in the research may suggest that the volatile components at cooking stage (I) were the representatives of the flavor volatiles of uncooked rice, while the volatile constituents at cooking stage (IV) were the representatives of the flavor volatiles of cooked rice.     

Amine degradation by 4,5-epoxy-2-decenal in model systems

The reactions of 4,5-epoxy-2-decenal with octylamine, benzylamine, and 2-phenylglycine methyl ester were studied to investigate if amines may suffer a Strecker type degradation by epoxyalkenals analogously to amino acids. In addition to other reactions, the studied amines were converted into their corresponding Strecker aldehydes (octanal, benzaldehyde, and methyl 2-oxo-2-phenylacetate, respectively) to an extent that depended on the pH, the temperature, the amount of epoxyalkenal, and the amine involved. Each amine exhibited an optimum pH for the reaction, but the corresponding Strecker aldehydes were produced to a significant extent within a broad pH range. In addition, the temperature mostly influenced the reaction rate, which was increased between 6.5 and 9.5 times when the reaction was carried out at 60 degrees C than when it took place at 37 degrees C. Furthermore, Strecker aldehyde formation was linearly correlated with the amount of the epoxyalkenal present in the reaction mixture. Nevertheless, the reaction yield mostly depended on the amine involved. Thus, octylamine only produced trace amounts of octanal, benzylamine was converted into benzaldehyde with a yield of 4.3%, and 2-phenylglycine methyl ester was converted into methyl 2-oxo-2-phenylacetate with a reaction yield of 49%. All of these results suggest that suitable amines can be degraded by epoxyalkenals to their corresponding Strecker aldehydes to a significant extent.     

自动化机械发酵食醋过程中品质变化规律

为全面了解转鼓式反应器固态发酵食醋过程中主要成分和风味物质的动态变化规律,该文对反应器发酵食醋过程进行跟踪取样,利用高效液相色谱、固相微萃取技术、气相色谱-质谱联用技术,对酒精、总酸、还原糖、氨基态氮、有机酸、挥发性风味物质含量变化进行实时监测,结合主成分分析方法,探究食醋不同发酵阶段的风味物质差异。结果表明,酒精含量在发酵0～4 d内迅速增加,随后逐渐下降至零;总酸含量呈现先快速上升后缓慢上升的趋势;还原糖含量呈先快速下降后逐渐上升,最后逐渐下降的趋势;氨基态氮呈现先快速上升后缓慢上升的趋势;乙酸和乳酸是主要的有机酸,整个发酵过程中,乙酸含量持续增加,乳酸含量呈先上升后下降趋势,其他有机酸含量较少,发酵期间变化波动相对较小;共检测出64种挥发性风味物质,包括酯类25种,醇类12种,酸类6种,酚类5种,醛类5种,酮类6种,杂环类5种;发酵前、中、后期的重要挥发性物质分别是醇类化合物、酯类和醛类化合物、酸类化合物。该结果为推进转鼓式固态发酵食醋反应器的实际生产应用提供了理论基础和数据参考。     

日光温室不同时段补光对番茄果实品质及挥发性物质影响

为探明日光温室中提高番茄产量和品质的最佳补光时段,以"粉太郎"番茄为试材,从植株定植后第25天到第一穗果完全成熟时进行补光,利用LED灯设置3种补光时段:揭帘前补光5 h(T1)、盖帘后补光5 h(T2)、揭帘前盖帘后分别补光2.5h(T3),以不补光作为对照(CK),研究其对番茄产量、果实品质以及挥发性物质成分和含量的影响。结果表明:补光处理可提高番茄平均单株产量、果实可溶性糖含量、可溶性固形物含量、糖酸比、挥发性物质总数量和总质量分数,但会降低有机酸含量,T1处理效果最显著(P<0.05)。4个处理共检测出83种挥发性物质,包括12种酮类、22种醛类、22种醇类、6种酯类、6种烃类和15种其他类物质。各处理挥发性物质总数量和总质量分数由大到小为:T1(68种,3 107.98μg/kg)、T3(65种,2 610.74μg/kg)、T2(63种,2 438.96μg/kg)、CK(59种,2 086.03μg/kg)。每个处理醇类含量最多,烃类含量最低,并且含量最高的物质均是顺-3-己烯-1-醇。3种补光处理均可提高酮类、醛类、醇类和其他类物质含量,但显著降低烃类物质含量(P<0.05),酯类物质含量只在T1处理时有所提高。所有被检测出的挥发性物质包含11种番茄特征香气成分,主要分为花香、果香与青香3种类型,其中青香味物质含量最多。综上,对番茄进行补光尤其是揭帘前补光5 h可有效提高番茄产量、果实品质和风味,是当地日光温室越冬茬番茄栽培的较优补光时段。研究结果可为设施番茄种植的光环境调控技术提供科学依据。